DE19620644A1 - Use of nitrogen-containing complexing agents for deodorization and antimicrobial treatment of the skin and textile fiber materials - Google Patents

Use of nitrogen-containing complexing agents for deodorization and antimicrobial treatment of the skin and textile fiber materials

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Publication number
DE19620644A1
DE19620644A1 DE19620644A DE19620644A DE19620644A1 DE 19620644 A1 DE19620644 A1 DE 19620644A1 DE 19620644 A DE19620644 A DE 19620644A DE 19620644 A DE19620644 A DE 19620644A DE 19620644 A1 DE19620644 A1 DE 19620644A1
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Prior art keywords
formula
carb2
complexing agents
carb3
complexing agent
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DE19620644A
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German (de)
Inventor
Frank Bachmann
Dietmar Ochs
Roland Utz
Thomas Ehlis
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Novartis AG
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Ciba Geigy AG
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Publication date
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Priority to DE19620644A priority Critical patent/DE19620644A1/en
Priority to EP97923037A priority patent/EP0901367A1/en
Priority to PCT/EP1997/002380 priority patent/WO1997044006A1/en
Priority to BR9709595-8A priority patent/BR9709595A/en
Priority to JP09541462A priority patent/JP2000511523A/en
Priority to US09/180,992 priority patent/US6391325B1/en
Priority to CN97194728A priority patent/CN1219124A/en
Priority to AU28951/97A priority patent/AU2895197A/en
Publication of DE19620644A1 publication Critical patent/DE19620644A1/en
Withdrawn legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • C11D9/30—Organic compounds, e.g. vitamins containing nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/005—Compositions containing perfumes; Compositions containing deodorants
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325—Amines
    • D06M13/342—Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/51—Chelating agents

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Environmental Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Zoology (AREA)
  • Birds (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cosmetics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)

Abstract

The present invention relates to the use of nitrogen-containing complexing agents for deodorization and antimicrobial treatment of the skin and of textile fibre materials. The complexing agents employed according to the invention have the formula (1), in which Q1 is Carb1; Carb2; or a radical of the formula (a); Q2 is hydrogen or Carb2; and Q3 is Carb3; an amino acid radical; or a radical of the formula (1a), where Carb1, Carb2 and Carb3 independently of one another are the radical of a C1-C8-mono- or -dicarboxylic acid and m1 is 1 to 5. The complexing agents according to the invention show a pronounced bacteriostatic action against Corynebacterium xerosis (bacteria which cause body odour) and are therefore suitable as the antimicrobial active substance in body care compositions and antimicrobial fabric finishing of textile materials.

Description

Die vorliegende Erfindung betrifft die Verwendung von stickstoffhaltigen Komplexbildnern zur Desodorierung und antimikrobiellen Behandlung der Haut und von textilen Faser­ materialien.The present invention relates to the use of nitrogen-containing complexing agents for deodorization and antimicrobial treatment of the skin and textile fibers materials.

Es ist bekannt, daß verschiedene stickstoffhaltige Komplexbildner, wie z. B. Ethylendiamin­ tetraessigsäure (EDTA), Nitrilotriessigsäure (NTA), β-Alanindiessigsäure (EDETA) oder Ethylendiamindibernsteinsäure (EDDS) in großem Umfang auf Grund ihrer komplex­ bildenden Eigenschaften in Haushaltswaschmitteln eingesetzt werden.It is known that various nitrogen-containing complexing agents, such as. B. ethylenediamine tetraacetic acid (EDTA), nitrilotriacetic acid (NTA), β-alaninediacetic acid (EDETA) or Ethylenediamine disuccinic acid (EDDS) on a large scale due to its complex forming properties are used in household detergents.

Überraschenderweise wurde gefunden, daß gewisse stickstoffhaltige Komplexbildner auch eine antimikrobielle Wirkung gegenüber grampositiven Bakterien haben und sich daher insbesondere zur Desodorierung und antimikrobiellen Behandlung der Haut und von textilen Fasermaterialien eignen.Surprisingly, it was found that certain nitrogen-containing complexing agents also have an antimicrobial effect against gram-positive bacteria therefore especially for deodorization and antimicrobial treatment of the skin and textile fiber materials are suitable.

Gegenstand der vorliegenden Erfindung ist daher die Verwendung von stickstoffhaltigen Komplexbildnern zur antimikrobiellen Behandlung der Haut und von textilen Faser­ materialien.The present invention therefore relates to the use of nitrogenous ones Complexing agents for the antimicrobial treatment of the skin and textile fibers materials.

Vorzugsweise werden erfindungsgemäß als Komplexbildner Verbindungen der FormelAccording to the invention, preference is given to compounds of the formula as complexing agents

worin
Q₁, Carb₁; Carb₂; oder einen Rest der Formel -(CH₂)m₁-OH
Q₂ Wasserstoff oder Carb₂; und
Q₃ Carb₃, einen Aminosäurerest; oder einen Rest der Formel (1a)wherein
Q₁, Carb₁; Carb₂; or a radical of the formula - (CH₂) m₁ -OH
Q₂ is hydrogen or Carb₂; and
Q₃ Carb₃, an amino acid residue; or a radical of the formula (1a)

bedeuten,
wobei Carb₁, Carb₂ und Carb₃ den Rest einer C₁-C₈-Mono- oder Dicarbonsäure; und
m₁ 1 bis 5 bedeuten,
verwendet.mean,
where Carb₁, Carb₂ and Carb₃ the rest of a C₁-C₈ mono- or dicarboxylic acid; and
m₁ is 1 to 5,
used.

Besonders bevorzugt sind dabei Verbindungen der Formel (1), worin der Aminosäurerest der FormelCompounds of the formula (1) in which the amino acid residue of the formula

entspricht; Carb₁ eine C₁-C₈-Dicarbonsäure, und Carb₂ und Carb₃ eine Monocarbonsäure bedeuten.corresponds; Carb₁ is a C₁-C₈ dicarboxylic acid, and Carb₂ and Carb₃ mean a monocarboxylic acid.

Von besonderem Interesse sind Komplexbildner der Formel (1), worin Carb₂ und Carb₃, unabhängig voneinander den Rest der FormelOf particular interest are complexing agents of the formula (1), in which Carb₂ and Carb₃, independently the rest of the formula

(1c) -[(CH₂)]n₁-COOH,(1c) - [(CH₂)] n₁ -COOH,

bedeuten, wobei
n₁ 0 bis 5 bedeutet.mean where
n₁ means 0 to 5.

Praktisch wichtige Komplexbildner entsprechen der FormelPractically important complexing agents correspond to the formula

oder der Formelor the formula

Weiterhin eignet sich Nitrilotriessigsäure (NTA) als Komplexbildner.Nitrilotriacetic acid (NTA) is also suitable as a complexing agent.

Weitere Beispiele für erfindungsgemäß einsetzbare Komplexbildner sind Amintri­ methylenphosphorsäure (ATMP) entsprechend der FormelAmintri are further examples of complexing agents which can be used according to the invention methylene phosphoric acid (ATMP) according to the formula

Serindiessigsäure (SDA) entsprechend der FormelSerine diacetic acid (SDA) according to the formula

Asparagindiessigsäure entsprechend der FormelAspartic diacetic acid according to the formula

oder
Methylglycindiessigsäure (MGDA) entsprechend der Formel (7)or
Methylglycinediacetic acid (MGDA) according to formula (7)

Die erfindungsgemäß eingesetzten stickstoffhaltigen Komplexbildner können nicht nur als Säure, sondern auch in Form ihrer wasserlöslichen Salze, vorzugsweise als Alkali- oder Ammoniumsalze eingesetzt werden.The nitrogen-containing complexing agents used according to the invention can not only be used as Acid, but also in the form of their water-soluble salts, preferably as alkali or Ammonium salts are used.

Ethylendiamindibernsteinsäure (EDDS) entsprechend Formel (2) hat zwei asymmetrische Kohlenstoffatome. Es sind daher verschiedene stereoisomere Formen dieser Verbindung möglich. Die (S,S)-Konfiguration von EDDS entspricht der FormelEthylenediamine disuccinic acid (EDDS) according to formula (2) has two asymmetrical ones Carbon atoms. There are therefore various stereoisomeric forms of this compound possible. The (S, S) configuration of EDDS corresponds to the formula

Eine kostengünstige chemische Synthese führt zu einem Gemisch der drei Formen S,S; R,R; und meso-EDDS. Die Auftrennung dieser stereoisomeren Verbindungen erfordert al­ lerdings einen großen technischen Aufwand. Optisch reines (S,S)-EDDS läßt sich mit Hilfe eines Actinomycetenstammes herstellten (T. Nishikiori et al., Production by Actinomycetes of (S,S)-N,N′-ethylenediaminedisuccinic acid, an inhibitor of phospholipase c; J.Antibiotics 37, 426-427 (1984)).An inexpensive chemical synthesis leads to a mixture of the three forms S, S; R, R; and meso-EDDS. The separation of these stereoisomeric compounds requires al but a great technical effort. Optically pure (S, S) EDDS can be used with the help of an Actinomycetes strain (T. Nishikiori et al., Production by Actinomycetes of (S, S) -N, N'-ethylenediaminedisuccinic acid, an inhibitor of phospholipase c; J. Antibiotics 37, 426-427 (1984)).

Die rein chemische Herstellung der Verbindung der Formel (4) erfolgt in an sich bekannter Weise, wie beispielsweise von J.A. Neal, N. Rose in Inorganic Chemistry,7, 2405 (1985) beschrieben ist.The purely chemical preparation of the compound of the formula (4) takes place in a manner known per se Manner, as for example by J.A. Neal, N. Rose in Inorganic Chemistry, 7, 2405 (1985) is described.

Racemisches EDDS läßt sich gem. US-Patentschrift 3,158,635 herstellen.Racemic EDDS can be gem. U.S. Patent 3,158,635.

Die erfindungsgemäßen Komplexbildner zeigen ausgeprägte bakteriostatische Wirkung, insbesondere gegen grampositive Bakterien der Hautflora, wie z. B. Corynebacterium xerosis (Bakterien, die Körpergeruch verursachen). Sie eignen sich daher insbesondere als antimikrobielle Wirksubstanz in Körperpflegemitteln, wie z. B. Seifen, Schampoos, Fußpflegeprodukten und insbesondere Deodoranten sowie als Zusatz in Waschmitteln.The complexing agents according to the invention show pronounced bacteriostatic activity, especially against gram-positive bacteria of the skin flora, such as. B. Corynebacterium xerosis (bacteria that cause body odor). They are therefore particularly suitable as antimicrobial active substance in personal care products, such as. B. soaps, shampoos, foot care products and in particular deodorants and as an additive in detergents.

Einen weiteren Erfindungsgegenstand bildet daher ein Körperpflegemittel, enthaltend mindestens einen Komplexbildner der Formel (1) sowie kosmetisch verträgliche Träger- oder Hilfsstoffe.A further subject of the invention therefore forms a personal care product containing at least one complexing agent of the formula (1) and cosmetically acceptable carrier or auxiliary substances.

Das erfindungsgemäße Körperpflegemittel enthält 0,1 bis 15, vorzugsweise 0,5 bis 10 Gew.-%, bezogen auf das Gesamtgewicht der Zusammensetzung, eines stickstoffhaltigen Komplexbildners und kosmetisch verträgliche Hilfsstoffe. The personal care product according to the invention contains 0.1 to 15, preferably 0.5 to 10 % By weight, based on the total weight of the composition, of a nitrogenous one Complexing agent and cosmetically compatible auxiliary substances.  

Je nachdem, in welcher Form das Körperpflegemittel vorliegt, weist es neben dem Komplexbildner noch weitere Bestandteile auf, wie z. B. Sequestriermittel, Farbstoffe, Parfümöle, Verdickungs- bzw. Festigungs(Konsistenzregler-)mittel, Emmollients, UV- Absorber, Hautschutzmittel, Antioxidantien, die mechanischen Eigenschaften verbessernde Additive wie Dicarbonsäuren und/oder Al-, Zn-, Ca-, Mg-Salze von C₁₄-C₂₂-Fettsäuren und gegebenenfalls Konservierungsmittel.Depending on the form of the personal care product, it shows next to the Complexing agents on other components, such as. B. sequestering agents, dyes, Perfume oils, thickening or strengthening (consistency regulator) agents, emmollients, UV Absorbers, skin protection agents, antioxidants, improving the mechanical properties Additives such as dicarboxylic acids and / or Al, Zn, Ca, Mg salts of C₁₄-C₂₂ fatty acids and optionally preservatives.

Die erfindungsgemäßen Komplexbildner lassen sich auf Grund ihrer guten Wasserlöslichkeit problemlos in die entsprechenden Formulierungen einarbeiten.The complexing agents according to the invention can be because of their good Easily incorporate water solubility into the corresponding formulations.

Das erfindungsgemäße Körperpflegemittel kann als Wasser-in-Öl- oder Öl-in-Wasser- Emulsion, als Öl-in-Alkohol-Lotion, als vesikulare Dispersion eines ionischen oder nicht­ ionischen amphiphilen Lipids, als Gel, fester Stift oder als Aerosol-Formulierung formuliert werden.The personal care product according to the invention can be used as a water-in-oil or oil-in-water Emulsion, as an oil-in-alcohol lotion, as a vesicular dispersion of an ionic or not ionic amphiphilic lipids, formulated as a gel, solid stick or as an aerosol formulation will.

Als Wasser-in-Öl- oder Öl-in-Wasser-Emulsion enthält der kosmetisch verträgliche Hilfsstoff vorzugsweise 5 bis 50% einer Ölphase, 5 bis 20% eines Emulgators und 30 bis 90% Wasser. Die Ölphase kann dabei irgendein für kosmetische Formulierungen geeignetes Öl enthalten, wie z. B. ein oder mehrere Kohlenwasserstofföle, ein Wachs, ein natürliches Öl, ein Silikon-Öl, einen Fettsäureester oder einen Fettalkohol. Bevorzugte Mono- oder Polyole sind Ethanol, Isopropanol, Propylenglykol, Hexylenglycol, Glycerin und Sorbitol.The cosmetically compatible auxiliary contains as a water-in-oil or oil-in-water emulsion preferably 5 to 50% of an oil phase, 5 to 20% of an emulsifier and 30 to 90% Water. The oil phase can be any oil suitable for cosmetic formulations included, such as B. one or more hydrocarbon oils, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol. Preferred mono- or polyols are ethanol, isopropanol, propylene glycol, hexylene glycol, glycerin and sorbitol.

Eine antimikrobielle Seife hat z. B. folgende Zusammensetzung:
0,01 bis 5 Gew.-% der Verbindung der Formel (2)
0,3 bis 1 Gew.-% Titandioxid,
1 bis 10 Gew.-% Stearinsäure
ad 100% Seifengrundlage, wie z. B. die Natriumsalze der Talgfett- und Kokosnußfettsäure oder Glycerine.An antimicrobial soap has e.g. B. The following composition:
0.01 to 5% by weight of the compound of the formula (2)
0.3 to 1% by weight of titanium dioxide,
1 to 10% by weight of stearic acid
ad 100% soap base, such as B. the sodium salts of tallow and coconut fatty acids or glycerols.

Ein Schampoo hat z. B. die folgende Zusammensetzung:
0,01 bis 5 Gew.-% der Verbindung der Formel (2),
12,0 Gew.-% Natrium-Laureth-2-sulfat,
4,0 Gew.-% Cocoamidopropylbetain,
3,0 Gew.-% NaCl und
Wasser ad 100%.A shampoo has e.g. B. the following composition:
0.01 to 5% by weight of the compound of the formula (2),
12.0% by weight sodium laureth-2-sulfate,
4.0% by weight cocoamidopropyl betaine,
3.0% by weight of NaCl and
Water ad 100%.

Ein Deodorant hat z. B. die folgende Zusammensetzung:
0,01 bis 5 Gew.-% der Verbindung der Formel (2),
60 Gew.-% Ethanol,
0,3 Gew.-% Parfümöl, und
Wasser ad 100%.A deodorant has e.g. B. the following composition:
0.01 to 5% by weight of the compound of the formula (2),
60% by weight ethanol,
0.3% by weight of perfume oil, and
Water ad 100%.

Weiterhin eignen sich die erfindungsgemäßen Komplexbildner für die Behandlung von textilen Fasermaterialien. Es handelt sich dabei um ungefärbte und gefärbte oder bedruck­ ten Fasermaterialien z. B. aus Seide, Leder, Wolle, Polyamid oder Polyurethanen, und insbesondere von cellulosehaltigen Fasermaterialien aller Art. Solche Fasermaterialien sind beispielsweise die natürliche Cellulosefaser, wie Baumwolle, Leinen, Jute und Hanf, sowie Zellstoff und regenerierte Cellulose. Bevorzugt sind textile Fasermaterialien aus Baumwolle.The complexing agents according to the invention are also suitable for the treatment of textile fiber materials. These are undyed and colored or printed ten fiber materials such. B. of silk, leather, wool, polyamide or polyurethane, and in particular of all types of cellulose-containing fiber materials. Such fiber materials are for example the natural cellulose fiber, such as cotton, linen, jute and hemp, and Pulp and regenerated cellulose. Textile fiber materials made of cotton are preferred.

Das folgende Beispiel dient zur Veranschaulichung der Erfindung.The following example serves to illustrate the invention.

Beispiel 1example 1 Bestimmung der antimikrobiellen Aktivitäten von S,S-EDDS, RR-EDDS, Racemat von EDDS und EDETA, EDTA und NTADetermination of the antimicrobial activities of S, S-EDDS, RR-EDDS, racemate by EDDS and EDETA, EDTA and NTA

Testmethode: Es wird ein Agarlochtest entsprechend der Methode CG 126 mit folgenden Modifikationen durchgeführt:
Medium: Casein-Sojamehlpepton Agar (Caso-Agar)
Testkeime: Corynebacterium xerosis ATCC 373
Corynebacterium xerosis ATCC 7711
Corynebacterium minutissimum ATCC 23358
Durchführung: 500 ml Caso-Agar werden mit 3,5 ml einer 1 : 100 verdünnten Übernachtkultur der Bakterien geimpft und Caso-Platten (18 ml) mit etwa 5 ml des bakterienhaltigen Agars überschichtet. Nach dem Erkalten der Planen werden mit einem Korkbohrer Löcher mit einem Durchmesser von 1 cm ausgestanzt. In jede Ausstanzung werden je 100 µl einer Testsubstanzverdünnung gefüllt und die Platten bei 37°C für 2 Tage inkubiert. Als Lösungsmittel wird für alle Substanzen bidestilliertes Wasser eingesetzt. Im Falle von EDETA GS wird der pH-Wert durch Zugabe von 1 N NaOH auf den pH-Wert von 3,3 eingestellt. Chemisch hergestelltes SS-EDDS wird durch Zugabe von 1 N NaOH auf den pH-Wert von 5,6 eingestellt.
Kontrollen: Bidestilliertes Wasser
Die Testergebnisse sind in Tabelle 1 aufgeführt:Test method: An agar hole test according to method CG 126 is carried out with the following modifications:
Medium: Casein soy flour peptone agar (Caso agar)
Test germs: Corynebacterium xerosis ATCC 373
Corynebacterium xerosis ATCC 7711
Corynebacterium minutissimum ATCC 23358
Procedure: Inoculate 500 ml Caso agar with 3.5 ml of a 1: 100 diluted overnight culture of the bacteria and overlay Caso plates (18 ml) with about 5 ml of the bacterial agar. After the tarpaulins have cooled, holes with a diameter of 1 cm are punched out with a cork drill. 100 μl of a test substance dilution are filled into each punch and the plates are incubated at 37 ° C. for 2 days. Double-distilled water is used as the solvent for all substances. In the case of EDETA GS, the pH is adjusted to 3.3 by adding 1 N NaOH. Chemically produced SS-EDDS is adjusted to a pH of 5.6 by adding 1 N NaOH.
Controls: distilled water
The test results are shown in Table 1:

Tabelle 1 Table 1

Die Testergebnisse zeigen, daß sowohl EDETA, EDTA und das fermentativ und chemisch hergestellte EDDS (=R,R; S,S; R,S)ausgeprägte bakteriostatische Wirkung gegen Coryne­ bacterium xerosis zeigen.The test results show that both EDETA, EDTA and the fermentative and chemical produced EDDS (= R, R; S, S; R, S) pronounced bacteriostatic effect against Coryne show bacterium xerosis.

Claims (12)

1. Verwendung von stickstoffhaltigen Komplexbildnern zur antimikrobiellen Behandlung der Haut und von textilen Fasermaterialien.1. Use of nitrogen-containing complexing agents for the antimicrobial treatment of Skin and textile fiber materials. 2. Verwendung nach Anspruch 1, dadurch gekennzeichnet, daß man als Komplexbildner Verbindungen der Formel worin
Q₁, Carb₁; Carb₂; oder einen Rest der Formel -(CH₂)m₁-OH;
Q₂ Wasserstoff oder Carb₂; und
Q₃ Carb₃, einen Aminosäurerest; oder einen Rest der Formel (1a) bedeuten,
wobei Carb₁, Carb₂ und Carb₃ den Rest einer C₁-C₈-Mono- oder Dicarbonsäure und
m₁ 1 bis 5 bedeuten, verwendet.2. Use according to claim 1, characterized in that compounds of the formula are used as complexing agents wherein
Q₁, Carb₁; Carb₂; or a radical of the formula - (CH₂) m₁ -OH;
Q₂ is hydrogen or Carb₂; and
Q₃ Carb₃, an amino acid residue; or a radical of the formula (1a) mean,
where Carb₁, Carb₂ and Carb₃ the rest of a C₁-C₈ mono- or dicarboxylic acid and
m₁ 1 to 5 mean used. 3. Verwendung nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß der Amino­ säurerest der Formel entspricht; Carb₁ eine C₁-C₈-Dicarbonsäure, und Carb₂ und Carb₃, unabhängig voneinander, eine Monocarbonsäure bedeuten. 3. Use according to claim 1 or 2, characterized in that the amino acid residue of the formula corresponds; Carb₁ is a C₁-C₈ dicarboxylic acid, and Carb₂ and Carb₃, independently of one another, are a monocarboxylic acid. 4. Verwendung nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß Carb₂ und Carb₃, unabhängig voneinander den Rest der Formel (1c) -[(CH₂)]n₁-COOH,bedeuten, worin
n₁ 0 bis 5 bedeutet.4. Use according to one of claims 1 to 3, characterized in that carb₂ and carb₃, independently of one another, denote the rest of the formula (1c) - [(CH₂)] n₁ -COOH, in which
n₁ means 0 to 5. 5. Verwendung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß man als Komplexbildner die Verbindung der Formel einsetzt.5. Use according to one of claims 1 to 4, characterized in that the compound of the formula as complexing agent starts. 6. Verwendung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß man als Komplexbildner die Verbindung der Formel einsetzt.6. Use according to any one of claims 1 to 4, characterized in that the compound of the formula is used as the complexing agent starts. 7. Verwendung nach Anspruch 1, dadurch gekennzeichnet, daß man als Komplexbildner Nitrilotriessigsäure verwendet.7. Use according to claim 1, characterized in that one as a complexing agent Nitrilotriacetic acid used. 8. Verwendung der Komplexbildner nach einem der Ansprüche 1 bis 7 als antimikrobielle Wirksubstanz gegen grampositive Bakterien.8. Use of the complexing agent according to one of claims 1 to 7 as an antimicrobial Active substance against gram-positive bacteria. 9. Verwendung der Komplexbildner nach einem der Ansprüche 1 bis 7 in Körperpflege­ mitteln.9. Use of the complexing agent according to one of claims 1 to 7 in personal care average. 10. Körperpflegemittel, enthaltend einen Komplexbildner der Formel (1) nach Anspruch 1. 10. Personal care product containing a complexing agent of formula (1) according to claim 1.   11. Körperpflegemittel gemäß Anspruch 10 in Form einer Seife, eines Schampoos oder eines Deodorants.11. Personal care product according to claim 10 in the form of a soap, a shampoo or a deodorant. 12. Verwendung der Komplexbildner nach einem der Ansprüche 1 bis 7 in textilen Fasermaterialien.12. Use of the complexing agent according to one of claims 1 to 7 in textiles Fiber materials.
DE19620644A 1996-05-22 1996-05-22 Use of nitrogen-containing complexing agents for deodorization and antimicrobial treatment of the skin and textile fiber materials Withdrawn DE19620644A1 (en)

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EP97923037A EP0901367A1 (en) 1996-05-22 1997-05-09 Use of nitrogen-containing complexing agents for deodorization and antimicrobial treatment of the skin and textile fibre materials
PCT/EP1997/002380 WO1997044006A1 (en) 1996-05-22 1997-05-09 Use of nitrogen-containing complexing agents for deodorization and antimicrobial treatment of the skin and textile fibre materials
BR9709595-8A BR9709595A (en) 1996-05-22 1997-05-09 Use of nitrogen-containing complexing agents for deodorization and antimicrobial treatment of skin and textile fiber materials
JP09541462A JP2000511523A (en) 1996-05-22 1997-05-09 Use of nitrogen-containing complexing agents for deodorizing and antibacterial treatment of skin and textile fibers
US09/180,992 US6391325B1 (en) 1996-05-22 1997-05-09 Use of nitrogen-containing complexing agents for deodorization and antimicrobial treatment of the skin and textile fibre materials
CN97194728A CN1219124A (en) 1996-05-22 1997-05-09 Use of nitrogen-containing complexing agents for deodorization and antimicrobial treatment of skin and textile fibre materials
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